An unprecedented electronic preference for the "meta" product in Diels-Alder reactions of ethynyldialkylboranes. [(Trimethylsilyl)ethynyl]-9-BBN as a reactive and versatile dienophile Academic Article uri icon


  • [(Trimethylsilyl)ethynyl]-9-BBN undergoes Diels–Alder reactions with acyclic dienes at 100 °C to afford 1,4-cyclohexadienes in high yields. The novel regiochemistry of these reactions is consistent with an ab initio prediction of advanced bonding to boron in a [4 atom + 3 atom] transition state. © 1992, American Chemical Society. All rights reserved.

altmetric score

  • 0.25

author list (cited authors)

  • Singleton, D. A., & Leung, S. W.

citation count

  • 41

publication date

  • August 1992